FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2005231805> ?p ?o ?g. }

• W2005231805 endingPage "822" @default.
• W2005231805 startingPage "813" @default.
• W2005231805 abstract "The synthesis of a novel chiral discriminating reagent, the ester resulting from the reaction of L-menthylphenylphosphoryl chloride with ethanol, is reported. This reagent, C, is aimed to differentiate the R and S monodeuterated enantiomers of ethanol, which constitutes an important isotopic probe for mechanistic studies and origin inference of natural products. The proportions of the two P-epimeric structures, CA and CB, which compose reagent C are directly accessible by 31P NMR. Analysis of 1D and 2D NMR spectra and theoretical simulations enable the 1H and 13C chemical shifts of CA and CB to be determined. The chemical shift differences exhibited by the methylenic hydrogens of the ethoxy moiety in CA and CB are of the order of 0.3 ppm. These large differences can be mainly attributed to ring current effects. Such effects have been estimated using two different methods on the basis of model conformations of the two epimers, CA and CB, deduced from energy minimization in a quantum mechanical approach. The relative signs of the chemical shift differences δR(C)—δS(C) associated with the pro-R and pro-S positions in the CA and CB isomers cannot be determined from the proton spectrum. The ring current calculations suggest that δR(C)—δS(C) are of opposite signs in the two P-epimers. This interpretation, and consequently the conformational analysis, are supported by the 2H NMR study of a chiral discriminating ester prepared from ethanol selectively enriched in deuterium in the pro-R position by stereospecific exchange reactions involving the enzymatic pair alcohol dehydrogenase–diaphorase. The chiral discriminating reagent, C, was then used for determining the enantiomeric imbalance in ethanol samples obtained from biosynthesis under different conditions, and site-specific fractionation factors were calculated." @default.
• W2005231805 created "2016-06-24" @default.
• W2005231805 creator A5006100995 @default.
• W2005231805 creator A5010072630 @default.
• W2005231805 creator A5031487016 @default.
• W2005231805 creator A5060629833 @default.
• W2005231805 creator A5064755915 @default.
• W2005231805 creator A5075900430 @default.
• W2005231805 date "1991-08-01" @default.
• W2005231805 modified "2023-10-18" @default.
• W2005231805 title "Monitoring site-specific natural hydrogen isotope fractionation using a novel phosphorus-containing chiral discriminating reagent" @default.
• W2005231805 cites W1966606663 @default.
• W2005231805 cites W1976008991 @default.
• W2005231805 cites W1976106600 @default.
• W2005231805 cites W1977768904 @default.
• W2005231805 cites W1991528768 @default.
• W2005231805 cites W2005114814 @default.
• W2005231805 cites W2006758647 @default.
• W2005231805 cites W2009878693 @default.
• W2005231805 cites W2012761622 @default.
• W2005231805 cites W2019510365 @default.
• W2005231805 cites W2022772618 @default.
• W2005231805 cites W2028669880 @default.
• W2005231805 cites W2035200848 @default.
• W2005231805 cites W2043966259 @default.
• W2005231805 cites W2048370530 @default.
• W2005231805 cites W2078718836 @default.
• W2005231805 cites W2090538233 @default.
• W2005231805 cites W2120439575 @default.
• W2005231805 cites W2168366928 @default.
• W2005231805 cites W2269758139 @default.
• W2005231805 cites W2312445213 @default.
• W2005231805 cites W2325706914 @default.
• W2005231805 cites W2328731388 @default.
• W2005231805 cites W1993314978 @default.
• W2005231805 doi "https://doi.org/10.1002/mrc.1260290812" @default.
• W2005231805 hasPublicationYear "1991" @default.
• W2005231805 type Work @default.
• W2005231805 sameAs 2005231805 @default.
• W2005231805 citedByCount "1" @default.
• W2005231805 crossrefType "journal-article" @default.
• W2005231805 hasAuthorship W2005231805A5006100995 @default.
• W2005231805 hasAuthorship W2005231805A5010072630 @default.
• W2005231805 hasAuthorship W2005231805A5031487016 @default.
• W2005231805 hasAuthorship W2005231805A5060629833 @default.
• W2005231805 hasAuthorship W2005231805A5064755915 @default.
• W2005231805 hasAuthorship W2005231805A5075900430 @default.
• W2005231805 hasConcept C103319777 @default.
• W2005231805 hasConcept C111429119 @default.
• W2005231805 hasConcept C121332964 @default.
• W2005231805 hasConcept C1276947 @default.
• W2005231805 hasConcept C147597530 @default.
• W2005231805 hasConcept C147789679 @default.
• W2005231805 hasConcept C161790260 @default.
• W2005231805 hasConcept C163111631 @default.
• W2005231805 hasConcept C178790620 @default.
• W2005231805 hasConcept C185592680 @default.
• W2005231805 hasConcept C187921627 @default.
• W2005231805 hasConcept C203130289 @default.
• W2005231805 hasConcept C2776568683 @default.
• W2005231805 hasConcept C40875361 @default.
• W2005231805 hasConcept C4839761 @default.
• W2005231805 hasConcept C486523 @default.
• W2005231805 hasConcept C58364064 @default.
• W2005231805 hasConcept C62520636 @default.
• W2005231805 hasConcept C67787023 @default.
• W2005231805 hasConcept C71240020 @default.
• W2005231805 hasConceptScore W2005231805C103319777 @default.
• W2005231805 hasConceptScore W2005231805C111429119 @default.
• W2005231805 hasConceptScore W2005231805C121332964 @default.
• W2005231805 hasConceptScore W2005231805C1276947 @default.
• W2005231805 hasConceptScore W2005231805C147597530 @default.
• W2005231805 hasConceptScore W2005231805C147789679 @default.
• W2005231805 hasConceptScore W2005231805C161790260 @default.
• W2005231805 hasConceptScore W2005231805C163111631 @default.
• W2005231805 hasConceptScore W2005231805C178790620 @default.
• W2005231805 hasConceptScore W2005231805C185592680 @default.
• W2005231805 hasConceptScore W2005231805C187921627 @default.
• W2005231805 hasConceptScore W2005231805C203130289 @default.
• W2005231805 hasConceptScore W2005231805C2776568683 @default.
• W2005231805 hasConceptScore W2005231805C40875361 @default.
• W2005231805 hasConceptScore W2005231805C4839761 @default.
• W2005231805 hasConceptScore W2005231805C486523 @default.
• W2005231805 hasConceptScore W2005231805C58364064 @default.
• W2005231805 hasConceptScore W2005231805C62520636 @default.
• W2005231805 hasConceptScore W2005231805C67787023 @default.
• W2005231805 hasConceptScore W2005231805C71240020 @default.
• W2005231805 hasIssue "8" @default.
• W2005231805 hasLocation W20052318051 @default.
• W2005231805 hasLocation W20052318052 @default.
• W2005231805 hasOpenAccess W2005231805 @default.
• W2005231805 hasPrimaryLocation W20052318051 @default.
• W2005231805 hasRelatedWork W1980952165 @default.
• W2005231805 hasRelatedWork W1982684003 @default.
• W2005231805 hasRelatedWork W2033747849 @default.
• W2005231805 hasRelatedWork W2056224812 @default.
• W2005231805 hasRelatedWork W2064037079 @default.
• W2005231805 hasRelatedWork W2091397225 @default.

• next